Quadrol, N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine, is often used as a cross-linking agent and catalyst in the synthesis of urethane foams and as an analytical reagent for the quantitative determination of Mn.sup.3+. Quadrol forms complexes with other polyvalent metal ions, e.g., cobalt, copper (II) and zinc. Recently applicants and coworkers have found that Quadrol possesses immunological activity. When mouse macrophages are exposed to Quadrol in vitro, the macrophages are rapidly stimulated as measured by increased phagocytosis and spreading. This stimulation was shown to be both time and concentration dependent. These findings were reported in M. V. Bhide et al, Journal of Immunopharmacology, vol. 7, no. 3, pp. 303-312 (1985).
Quadrol can be prepared by reacting one mol of ethylenediamine with 4 mols of propylene oxide as described in U.S. Pat. No. 2,697,113 to Lundsted et al.
U.S. Pat. No. 3,868,409 discloses, inter alia, the monomers obtained by reacting either 3 or 4 moles of glycidyl methacrylate with ethylenediamine, and polymers thereof. The monomers are trifunctional or tetrafunctional, depending on the number of moles of glycidyl methacrylate reacted, and are capable of a high degree of cross-linking. Polymers formed from these monomers are highly cross-linked, rigid and brittle. Also disclosed are other polymers formed by reaction of glycidyl methacrylate and other epoxy compounds with various monoamines, diamines and polyamines. Patentee characterizes his polymers as having exceptionally high strength, and as bonding strongly to metals.
Hydrogel polymers of certain methacrylate monomers, notably 2-hydroxyethyl methacrylate (HEMA), are well known. HEMA polymers are widely used in the manufacture of contact lenses and also have been reported as being useful in other biomedical and surgical applications. HEMA is capable of homopolymerizing and copolymerizing with other methacrylates to form three-dimensional hydrophilic polymer (hydrogel) networks. References disclosing HEMA polymers include, for example, D. E. Gregonis et al., "Hydrogels For Medical And Related Applications", American Chemical Society Symposium, Series No. 31, edited by J. D. Andrade, August 1976, pages 88-104, and M. F. Refojo et al, Journal of Applied Polymer Science, vol. 9, pages 2425-2435 (1965). M. F. Refojo, J. Applied Polymer Sci., vol. 9, pp 3161-3170 (1965) discloses hydrogels prepared from glyceryl methacrylate.
U.S. Pat. No. 3,220,960 to Wichterle et al discloses hydrogels consisting essentially of 20-97 percent of an aqueous liquid and a cross-linked hydrophilic polymer. Use for hydrogels obtained from various derivatives of acrylic and methacrylic acids include dialysis membranes, diaphragms, contact lenses and other uses where prolonged contact with body tissues is required.
Wound dressings incorporating certain hydrogels have been described in the literature. Agar-acrylamide hydrogels and their use in wound dressings are described, for example in B. Kickhoefer et al., Biomaterials, vol. 7, pages 67-72 (1986).